US3042686A - Epoxydicyclopentyl alcohols and process for preparing same - Google Patents

Epoxydicyclopentyl alcohols and process for preparing same Download PDF

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US3042686A
US3042686A US13986A US1398660A US3042686A US 3042686 A US3042686 A US 3042686A US 13986 A US13986 A US 13986A US 1398660 A US1398660 A US 1398660A US 3042686 A US3042686 A US 3042686A
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grams
epoxydicyclopentyl
alcohols
ether
oxirane oxygen
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US13986A
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Joseph L O'brien
Constance A Lane
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Rohm and Haas Co
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/22—Ethers with hydroxy compounds containing no oxirane rings with monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/14—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
    • C07D303/02—Compounds containing oxirane rings
    • C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
    • C07D303/18—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by etherified hydroxyl radicals
    • C07D303/20—Ethers with hydroxy compounds containing no oxirane rings
    • C07D303/24—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds
    • C07D303/26—Ethers with hydroxy compounds containing no oxirane rings with polyhydroxy compounds having one or more free hydroxyl radicals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/145—Compounds containing one epoxy group
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
    • C08G59/22—Di-epoxy compounds
    • C08G59/24—Di-epoxy compounds carbocyclic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
    • C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
    • C08G59/42—Polycarboxylic acids; Anhydrides, halides or low molecular weight esters thereof

Definitions

  • This invention relates to a new class of epoxy alcohols derived from dicyclopentadiene. More particularly it relates to epoxydicyciopentyl alcohols and to their preparation by epoxidation of the corresponding dicyclopentenyl alcohols.
  • the olefinic alcohols used as starting materials in accordance with this invention are prepared according to the process disclosed in United States Patent No. 2,385,788 or in United States Patent No. 2,393,609.
  • the new epoxy alcohols may be represented by the following general formula:
  • n is an integer having a value of 1 to 5, inelusive.
  • Epoxyclicyclopentyl alcohol m0 CHzCHaOH Epoxydicyclopentyloxyethanol @OCHzCl-IzOCHaCHzOH Epoxydicyclopentyloxyethoxyethanol
  • Triethylene glycol monoepoxydicyclopentyl ether Tetraethylene glycol monoepoxydicyclopentyl ether a 40% solution in glacial acetic acid, may beemployed for the process of this invention. About 3% by weight of sodium acetate is added to removed the sulfuric acid normally present in the commercial reagent.
  • Other peracids that may be employed are performic acid, perrbenzoic acid, monoperphthalic acid, and the like.
  • the compounds of this invention are useful as reactive modifiers for epoxy resins to obtain resin systems of reduced viscosity and for the preparation of polymeric resins by reaction with polycarboxylic anhydrides in the presence of acidic catalysts.
  • EXAMPLE 1 Preparation of Epoxydicyclopentyl Alcohol To grams of dicyclopentenyl alcohol in 300 ml. of anhydrous benzene there was added, over a period of thirty minutes, 139 grams of a 40% solution of peracetic acid in glacial acetic acid, containing 4.2 grams of anhydrous sodium acetate. The temperature was maintained at 45-50 C. with stirring for an additional four hours. Upon cooling to 30 C., brine (400 ml.) was added and the solution was extracted twice with benzene. The combined benzene extract was washed with brine and 5% aqueous sodium carbonate solution, saturated with sodium chloride, until neutral.
  • EXAMPLE 2 Preparation of Epoxydicyclopentyloxyethanol A solution of grams of 40% peracetic acid in glacial acetic acid, containing 4.2 grams of anhydrous sodium acetate, was added to 97 grams of hydroxyethyl dicyclopentenyl ether in 300 ml. of benzene at 45-50 C. in thirty minutes. Stirring was continued at 45-50 C. for an additional four hours. Upon cooling to 30 C., brine (250 ml.) was added and the solution extracted twice with benzene. The combined benzene extract was then neutralized by washing with brine and aqueous carbonate solution, dried over mangesium sulfate and stripped to 100 C./40 mm.
  • EXAMPLE 6 Compositions of Epoxydicyclopentyl Alcohol With Bis- Epoxides and :Polycizrboxylic Acid' Anhydrides
  • the bis-epoxide used in this example is the bis-epoxydicyclopentyl ether of ethylene glycol, designated AG- 13E, and prepared in accordance with the teaching of United States Patent No..2,543',419.
  • This material is a waxy solid which forms relatively viscous mixtures with polycarboxylic acid anhydridesr Addition of epoxydicyclopentyl alcohol results in a less viscous resin which shows. a more moderate exotherm when cured in the presence of acidic catalysts.
  • n is an integer having a value of l to 5, inclusive.
  • Epoxydicyclopentyl alcohol of the formula 5. Triethylene glycol monoepoxydicyclopentyl ether of the formula monoepoxydicyclopentyl ether 6. Tetraethylene glycol of the formula oh, o owmomopn References Cited in the file of this patent UNITED STATES PATENTS Niederhauser Feb. 27, 1951 Buchner et al. Apr. 7, v1959 Notice of Adverse Decision in Interference In Interference N 0. 93,992 involvin Patent N 0. 3,042,686, J. L.

Description

EPQXYDICYCLGPENTYL ALCGHQLS AND PRGC- ESS FOR PREPG SAME Joseph L. GBrien, Elkins Park, and Constance A. Lane, Philadelphia, 1 2., assignors to Rohm & Haas Company, Philadelphia, Pa, a corporation of Delaware No Drawing. Filed 10, 1960, Ser. No. 13,986 6 Claims. ((11. 260-348) This invention relates to a new class of epoxy alcohols derived from dicyclopentadiene. More particularly it relates to epoxydicyciopentyl alcohols and to their preparation by epoxidation of the corresponding dicyclopentenyl alcohols. The olefinic alcohols used as starting materials in accordance with this invention are prepared according to the process disclosed in United States Patent No. 2,385,788 or in United States Patent No. 2,393,609.
The new epoxy alcohols may be represented by the following general formula:
wherein n is an integer having a value of 1 to 5, inelusive.
Typical of compounds within the scope of this invention are the following:
Epoxyclicyclopentyl alcohol m0 CHzCHaOH Epoxydicyclopentyloxyethanol @OCHzCl-IzOCHaCHzOH Epoxydicyclopentyloxyethoxyethanol Triethylene glycol monoepoxydicyclopentyl ether Tetraethylene glycol monoepoxydicyclopentyl ether a 40% solution in glacial acetic acid, may beemployed for the process of this invention. About 3% by weight of sodium acetate is added to removed the sulfuric acid normally present in the commercial reagent. Other peracids that may be employed are performic acid, perrbenzoic acid, monoperphthalic acid, and the like.
The compounds of this invention are useful as reactive modifiers for epoxy resins to obtain resin systems of reduced viscosity and for the preparation of polymeric resins by reaction with polycarboxylic anhydrides in the presence of acidic catalysts.
The following examples serve to illustrate this invention.
EXAMPLE 1 Preparation of Epoxydicyclopentyl Alcohol To grams of dicyclopentenyl alcohol in 300 ml. of anhydrous benzene there was added, over a period of thirty minutes, 139 grams of a 40% solution of peracetic acid in glacial acetic acid, containing 4.2 grams of anhydrous sodium acetate. The temperature was maintained at 45-50 C. with stirring for an additional four hours. Upon cooling to 30 C., brine (400 ml.) was added and the solution was extracted twice with benzene. The combined benzene extract was washed with brine and 5% aqueous sodium carbonate solution, saturated with sodium chloride, until neutral. After drying over magnesium sulfate and stripping free of solvent to 100 C./40 mm., there remained 98.5 grams (89% yield) of a pale yellow oil. Distillation gave 91.5 grams (82.5% yield) of a single product distilling at AIS-20 C./.04 mm., n =1.5l55.
Analysis-Calculated for C H O =C, 72.25%; H, 8.49%; oxirane oxygen, 9.63%. Found: C, 72.78%; 8.68%; oxirane oxygen, 9.0%.
The infrared spectrum of this product showed absorption bands characteristic of the hydroxyl group and oxirane ring, in accordance with the assigned structure.
EXAMPLE 2 Preparation of Epoxydicyclopentyloxyethanol A solution of grams of 40% peracetic acid in glacial acetic acid, containing 4.2 grams of anhydrous sodium acetate, was added to 97 grams of hydroxyethyl dicyclopentenyl ether in 300 ml. of benzene at 45-50 C. in thirty minutes. Stirring was continued at 45-50 C. for an additional four hours. Upon cooling to 30 C., brine (250 ml.) was added and the solution extracted twice with benzene. The combined benzene extract was then neutralized by washing with brine and aqueous carbonate solution, dried over mangesium sulfate and stripped to 100 C./40 mm. There remained 99 grams (94% yield) of crude product having an oxirane oxygen content of 6.97% and n =1.51l7. Distillation gave 89 grams (85% yield) of a colorless oil, distilling at- C./.03 mm., n =l.5lO6.
-Analysis.Calculated for C H O C, 68.54%; H, 8.63%; oxirane oxygen, 7.61%. Found: C, 68.76%; H, 8.62%; oxirane oxygen, 7.0%. v I
The infrared spectrum of this sample was in accordance with the assigned structure.
EXAMPLE 3 Preparation of Epoxydicyclopentyloxyethoxyethanol To 119 grams of hydroxyethoxyethyl dicyclopentenyl ether in 400 ml. of anhydrous benzene, there was added 105 grams of 40% peracetic acid in glacial acetic acid, containing 4.2 grams of anhydrous sodium acetate. After an addition period of thirty minutes, stirring was continued at 4550 C. for an additional four hours. Upon cooling to room temperature, the solution was diluted with brine and extracted with benzene. The benzene extract was washed with brine and aqueous carbonate solution until neutral, dried over magnesium sulfate and stripped to 100 C./40 mm. There remained .125 grams (98.5% yield) of the crude product having 11 1.5073 and 5.95% ,oxirane oxygen. Distillation gave 98 grams (77%. yield) of a colorless oil distilling at l607 C./0.06 mm., n =-1.5041.-
Analysis.-Calculated for C H O C, 66.11%; .H, 8.72%; oxirane oxygen, 6.29%. Found: C, 66.37%; H, 8.63%; oxirane oxygen, 6.65%.
The infrared spectrum of this sample was in accord with the assigned structure.
EXAMPLE 4 Preparation of Triethylene Glycol Monoepoxydicyclopentyl Ether By a procedure similar to that employed in Example 1, 141 grams of triethylene glycol monodicyclopentenyl ether gave 143 grams (96% yield) of crude product havmg n,;, 1.4993 and 4.93% oxirane oxygen. Distillation yielded 117 grams of a colorless oil, distilling at 180- 190 C./.06 mm., n =1.49*80.
Analysis-Calculated for C H O C, 64.41%; H, 8.78%; oxirane oxygen, 5.36%; Found:' C, 64.85%; H, 8.79%; oxirane oxygen, 5.2%.
The infrared spectrum of this sample was in accordance with the assigned structure.
EXAMPLE 5 Preparation of Tetraethylene Glycol Monoepoxydicyclo'pentyl Ether EA similar procedure to thatused in, Example 1 was followed using 33 grams of tetraethylene glycol monodicyelopentenylv ether. Itv gave 325 grams (95% yield) of crude product having 11 1.5004 and 4.56% oxirane 7 oxygen. Distillation yielded 21 grams of a clear,;yellow oil distilling at ZOO-235 C./'.050.20 mm., n :1.5024. Analysis.Calculated for ;C H O C, 63.14%; H, 8.83%; oxirane oxygen, 4.67.%. Found: C, 64.13%; H, 8.60%; oxirane oxygen, 4.8%. a
- The infrared spectrum of thissample was in accordance withthe assigned structure.
. EXAMPLE 6 Compositions of Epoxydicyclopentyl Alcohol With Bis- Epoxides and :Polycizrboxylic Acid' Anhydrides The bis-epoxide used in this example is the bis-epoxydicyclopentyl ether of ethylene glycol, designated AG- 13E, and prepared in accordance with the teaching of United States Patent No..2,543',419. This material is a waxy solid which forms relatively viscous mixtures with polycarboxylic acid anhydridesr Addition of epoxydicyclopentyl alcohol results in a less viscous resin which shows. a more moderate exotherm when cured in the presence of acidic catalysts. To a mixture of 144 parts of AG-13-E, 17 parts of epoxydicyclopentyl alcohol, and 57 parts of methylsuccinic anhydride was added 1% by weight of a 50% aqueous solution of cadmium fluoborate. There was a mild exotherm as .the mixture was stirred and a thick gel formed five minutes. The gel was heated for two hours at 80 C. and then for 16 hours at 120 C. A clear amber resin having a Barcol hardness of was obtained.
Other commercial vepoxy resins and other polycar 5 boxylic acid anhydrides were reacted with epoxydicyclopentyl alcohol in the above manner with substantially the same results.
We claim: a 1. A compound of the formula CH, CH
wherein n is an integer having a value of l to 5, inclusive.
2. Epoxydicyclopentyl alcohol of the formula 5. Triethylene glycol monoepoxydicyclopentyl ether of the formula monoepoxydicyclopentyl ether 6. Tetraethylene glycol of the formula oh, o owmomopn References Cited in the file of this patent UNITED STATES PATENTS Niederhauser Feb. 27, 1951 Buchner et al. Apr. 7, v1959 Notice of Adverse Decision in Interference In Interference N 0. 93,992 involvin Patent N 0. 3,042,686, J. L. OBrien O A, Lane, EPOXYDIGYCLOPfiNTYL ALCOHOLS AND PROC- PREPARING sAME final judgment adverse to the patentees July 30, 1965, as to claims 1, 2 and 3. [OJfioiaZ Gazette September 28, 1965.]

Claims (1)

1. A COMPOUND OF THE FORMULA WHEREIN N IS AN INTEGER HAVING A VALUE OF 1 TO 5, INCLUSIVE.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3225115A (en) * 1960-12-28 1965-12-21 Union Carbide Corp Curable compositions containing epoxy alcohol, unsaturated polycarboxylic acid and unsaturated monomer
US3247137A (en) * 1960-12-28 1966-04-19 Union Carbide Corp Polymer of a monoepoxy alcohol and reaction products thereof
US3264271A (en) * 1961-03-27 1966-08-02 Ciba Ltd Heat-curable mixtures of epoxy derivatives and polycarboxylic acid anhydrides
US3280152A (en) * 1960-09-13 1966-10-18 Union Carbide Corp Epoxy alcohol compounds
US3329502A (en) * 1963-10-01 1967-07-04 American Cyanamid Co Epoxide compounds and photochromic compositions containing the same
US3340213A (en) * 1964-05-19 1967-09-05 Union Carbide Corp Coating compositions from monoepoxy alcohols
US3341484A (en) * 1964-05-19 1967-09-12 Union Carbide Corp Varnishes prepared from novel copolymers of monoepoxy alcohols and monoepoxides
US3392129A (en) * 1965-01-07 1968-07-09 Union Carbide Corp Ester polyol-carboxylic acid adducts and water-based paint compositions therefrom
US3405100A (en) * 1960-04-05 1968-10-08 Ciba Ltd Esters containing epoxide groups, their production and their uses
US3428612A (en) * 1960-10-05 1969-02-18 Union Carbide Corp Diepoxide compositions
US3440192A (en) * 1964-10-05 1969-04-22 Union Carbide Corp Polyester-carboxylic acid adducts and water-based paint compositions therefrom
US3541114A (en) * 1967-01-13 1970-11-17 Celanese Corp Recovery of hydrophobic oxirane compounds
US4622349A (en) * 1983-02-07 1986-11-11 Union Carbide Corporation Blends of epoxides and monoepoxides
US4814361A (en) * 1983-02-07 1989-03-21 Union Carbide Corporation Blends of epoxides and monoepoxides

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2543419A (en) * 1949-05-11 1951-02-27 Rohm & Haas Polycyclic di-epoxy ethers
US2881208A (en) * 1955-08-18 1959-04-07 Ruhrchemie Ag Di-tricyclodecane (5, 2, 1, 02, 6)-8, 8'-ether-4, 4'-dicarboxylic acid

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2543419A (en) * 1949-05-11 1951-02-27 Rohm & Haas Polycyclic di-epoxy ethers
US2881208A (en) * 1955-08-18 1959-04-07 Ruhrchemie Ag Di-tricyclodecane (5, 2, 1, 02, 6)-8, 8'-ether-4, 4'-dicarboxylic acid

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3405100A (en) * 1960-04-05 1968-10-08 Ciba Ltd Esters containing epoxide groups, their production and their uses
US3280152A (en) * 1960-09-13 1966-10-18 Union Carbide Corp Epoxy alcohol compounds
US3428612A (en) * 1960-10-05 1969-02-18 Union Carbide Corp Diepoxide compositions
US3225115A (en) * 1960-12-28 1965-12-21 Union Carbide Corp Curable compositions containing epoxy alcohol, unsaturated polycarboxylic acid and unsaturated monomer
US3247137A (en) * 1960-12-28 1966-04-19 Union Carbide Corp Polymer of a monoepoxy alcohol and reaction products thereof
US3153003A (en) * 1961-02-23 1964-10-13 Rohm & Haas Aqueous dispersion of an aminoplast and an epoxy compound
US3264271A (en) * 1961-03-27 1966-08-02 Ciba Ltd Heat-curable mixtures of epoxy derivatives and polycarboxylic acid anhydrides
US3329502A (en) * 1963-10-01 1967-07-04 American Cyanamid Co Epoxide compounds and photochromic compositions containing the same
US3341484A (en) * 1964-05-19 1967-09-12 Union Carbide Corp Varnishes prepared from novel copolymers of monoepoxy alcohols and monoepoxides
US3340213A (en) * 1964-05-19 1967-09-05 Union Carbide Corp Coating compositions from monoepoxy alcohols
US3440192A (en) * 1964-10-05 1969-04-22 Union Carbide Corp Polyester-carboxylic acid adducts and water-based paint compositions therefrom
US3392129A (en) * 1965-01-07 1968-07-09 Union Carbide Corp Ester polyol-carboxylic acid adducts and water-based paint compositions therefrom
US3541114A (en) * 1967-01-13 1970-11-17 Celanese Corp Recovery of hydrophobic oxirane compounds
US4622349A (en) * 1983-02-07 1986-11-11 Union Carbide Corporation Blends of epoxides and monoepoxides
US4814361A (en) * 1983-02-07 1989-03-21 Union Carbide Corporation Blends of epoxides and monoepoxides

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